Promoting color change in human hair with a dialdehyde compound and a nitrogen containing compound

ABSTRACT

A method for promoting color change in human hair by impregnating the hair with a solution containing at least one dialdehyde compound in combination with at least one nitrogen containing compound and allowing the solution to remain in contact with the hair for an effective period of time to permit the desired color to develop. The use of dialdehyde promoting compounds have been found to generate the desired color in a much shorter period of time than heretofore known, and yield good development of the desired color shades.

United States Patent I Kinney et al.

[ Mar. 18, 1975 Antoni Edward Gadzala, Suffern, NY.

[73] Assignee: Avon Products, Inc., Suffern, NY.

[22] Filed: Apr. 11, I973 [21] Appl. No.: 350,170

Related U.S. Application Data [63] Continuation-impart of Ser. No. 301,785, Oct. 30,

[52] U.S. Cl. 8/10.2, 8/11 [51] Int. Cl A6Ik 7/12 [58] Field of Search 8/10.2, 11; 96/100 [56] References Cited UNITED STATES PATENTS 2,948,756 8/1960 Bengelsdorf 260/599 3,102,811 9/1963 Barney 96/48 R 3,781,418 12/1973 Pomot et al. 424/63 FOREIGN PATENTS OR APPLICATIONS 401,361 4/1966 Switzerland 8/l0.2

Primary Examiner-Albert T. Meyers Assistant Examiner-Vera C. Clarke Attorney, Agent, or F irmPennie & Edmonds [57] ABSTRACT A method for promoting color change in human hair by impregnating the hair with a solution containing at least one dialdehyde compound in combination with at least one nitrogen containing compound and allowing the solution to remain in contact with the hair for an effective period of time to permit the desired color to develop The use of dialdehyde'promoting compounds have been found to generate the desired color in a much shorter period of time than heretofore known, and yield good development of the desired color shades. v

9 Claims, N0 Drawings REFERENCE TO RELATED APPLICATION This is a continuation-in-part of copending application Ser. No. 301,785, filed Oct. 30, I972.

BACKGROUND OF THE INVENTION For many years people have been dissatisfied with the natural coloration of the human hair and have sought preparations capable of modifying the colors. Numerous color modifying materials and many varied procedures for applying such materials have been developed in attempts to formulate coloring techniques which will quickly attain the desired color and to facilitate the ease of dyeing to various desired color combinations.

Generally, the various methods of dyeing hair fibers includes absorption, aggregation and bonding techniques. When direct bonding techniques are utilized on human hair, a true chemical bond is formed between the dye material and the treated hair fiber. The dye must have a reactive group which can chemically bond with one of the groups present on the hair fiber. The use of reactive dyes which form chemical bonds with the hair fibers have generally been limited due to the severe conditions which are needed to force the 'reaction to occur.

In general, human hair has been colored by the use of the absorption or aggregation techniques. In the absorption method the dyestuff or the vehicle in which it is introduced has an-electrode affinity for the hair fiber being treated. This technique relies primarily onthe charge differential between the various materials and normally can be done under conditions which are suitable for cosmetic purposes. Similarly, the aggregation method of dyeing involves a system of insolubility which is created inside the fiber to be dyed. The dye material is made fast by penetration into the fiber and the precipitation therein of the chromogenous agent.

In the absorption and aggregation methods it has been found advantageous to include a dye promoting material which enhances the dye uptake onto the hair fibers. Various chemical compounds, including certain aromatic and aliphatic diketones, have been found useful in increasing the dye uptake of various known coloring agents. Normally, these dye promoting materials act to enhance the uptake of the hair dyeing compositions and thus reduce the time needed to form an effective dyeing of the human hair. In other cases dye pr0- moting materials have been used to lessen the drastic conditions sometimes found necessary to form the desired coloration of the hair.

The various color promoting materials, such as the diketones mentioned above, have been limited as to color shades they will promote and the rate of promoting the dye uptake.

SUMMARY OF THE INVENTION It has been presently unexpectedly found that dyeing of human hair can be enhanced and promoted by impregnating hair with a phurmacologically acceptable carrier material containing one or more dialdehyde compounds of the general formula:

in which R represents a divalent aromatic, cycloaliphatic or aliphatic group. The dialdehyde compounds of this invention have been found to rapidly promote the dyeing of human hair when accompanied by at least one nitrogen containing compound.

The preferred embodiment being found that ortho or paraphthalaldehyde rapidly promotes coloration of human hair when used in combination with at least one nitrogen containing compound of the group consisting of monoalkanolamine, dialkanolamine, trialkanolamine, alkyl monoalkanolamine, dialkyl monoalkanolamine, alkyldialkanolamine and ammonium hydroxide.

DETAILED DESCRIPTION OF THE INVENTION The present invention provides a composition and a process for dyeing hair which comprises impregnating the hair with a solution, emulsion, or dispersion containing one or more dialdehyde compounds described hereinbelow in combination with the necessary nitrogen containing material which is color promoted.

A unique class of compounds for promoting of color changes human hair has been found to consist of compounds having the general formulaz M 0 0 Lib-1.

in which R represents. a divalent aromatic, cycloaliphatic or aliphatic group and in which n equals 0 or 1. When n equals 0, the dialdehyde of this invention is glyoxal. When :1 equals 1, a suitable divalent bridging radical is present and represented by R.'Such radicals may be alkylene, arylene and cycloalkylene groupings including methylene, ethylene, propylene, butylene, pentarnethylene, I

- JFH:

and the like. The dialdehyde compounds of this invention may be used singly or in combination. The use of the particular dialdehydes will depend upon the solubility in the carrier material.

Particularly suitable as the dye promoting compound is ortho, meta and para phthalaldehyde. These compounds have been found to give extremely fast uptake and fastness to a wide variety of dyes useful in absorption and aggregation techniques. In addition to the above aldehyde compounds,one may include various other organicpromoting materials including phthalimides and the like.

Furthermore, the use of ortho, meta or para phthalald'ehyde in combination with at least one nitrogen containing compound, as herein described below, has been found to give extremely fast color change which has good fastness properties. The hard to come by rich black, and blue-gray shades are easily attained in thisman'ner.. I

The concentration of 'the promoting material may range from about 0.05 to about per cent of the total composition being applied to the hair with from about 0.1 to about 0.5 per cent being preferred. Concentrations higher than this have been, in most cases, found economically unfeasible. The additional promoting materials which may be used in combination with the dialdehydes may be in concentrations ranging from about 0.1 to about 5 per cent of the total weight of the composition.

. The dialdehyde promoting compounds, ortho, meta and para phthalaldehyde, have been found to give extremely fast color change whenused in combination with a nitrogen containing compound selected from the group consisting of monoalkanolamine, dialkanolamine, trialkanolamine, alkyl monoalkanolamine, dialkylalkanolamine, alkyl dialkanolamine and ammonium hydroxide and the like. The alkanol radical of said nitrogen containing compounds may be any C C alkanol group, such as methanol, ethanol and the like and the alkyl group of said compounds may be any C C alkyl group, such as methyl, ethyl, decyl, lauryl and the like. The concentration of these compounds may range from about .1 to per cent with from about 0.5 to 5 per cent preferred.

The use of the dialdehyde compound herein above described has been found to yield extremely fast color treatment when used in combination with a nitrogen containing compound. Normally, the hair being treated may be contacted with the combination of at least one of such nitrogen compounds and the dialdehyde promoter for less than 5 minutes to yield the desired color change. Normally, the desired color is attained in from about 1 to about 4 minutes. The exact color produced in both a function of time of application and of the particular combination of reactive materials used and such color can be readily determined by ordinary procedures.

The process of this invention may be carried out by contacting the hair first with a solution, dispersion or emulsion containing the dialdehyde and allowed to remain on the hair for a time sufficient to permit penetration of the hair. Normally from about 1 to about 5 minutes in duration is sufficient. The hair is then permitted to be treated with a solution containing the desired nitrogen containing material. The order of application of the reactive materials may be reversed. Alternately, the nitrogen containing material and the dialdehyde material may be applied to the hair in the same solution. When applied in this manner, it normally will cause the desired color change within a time of less than 5 minutes.

The dialdehyde-nitrogen compound composition as disclosed herein rapidly produces color changes in human hair. The exact rate of development depends on the particular combination of compounds used and the pH of the resultant composition and can be easily determined by routine procedures. in general, it is found 4 that dialdehyde-nitrogen compositions produce the deepest colors most readily at pH ranges of 4 to 7.

The nitrogen containing material in combination with the dialdehyde promoter herein disclosed is rinsed free ofthe hair after producing the desired color change. These spent materials may be washed free with water or with any commercially available shampoo to allow the hair to have the dyed, color within'a relatively short period of time and to produce a dyed hair which has remarkable fastness and reproducible results.

' It has also'beenfound that shades of silver to black which have here'tofore'beenfound unsuitable :for absorption and aggregation hair coloring techniques are suitably promoted when a dialdehyde and a nitrogen compound, 'such as para-phenylenediamine, trialkanolamine, NH OH and the like are used.

The dialdehyde material in combination with the nitrogen containing compound is generally applied to the hair in the form of an aqueoussolution, dispersion or emulsion. Any pharmaceutically acceptable carrier base, such as water or an aqueous shampoo solution, may be used as a carrier material for application-of the essential ingredients on the hair. The essential ingredi ents in combination with such carrier materials are allowed to remain on the hair for a length of time necessary for producing the desired color change. Depending on the hairs porosity, such time is normally from about 1 to about 4 minutes and normally less than 5 minutes in time has been found acceptable. The hair is then rinsed free of the spent materials with warm water and may be washed with any commercial shampoo in order to remove residual materials. Additional solvents, such as alcohols, preferably lower alcohols, such as methanol, ethanol, isopropanol, and the like alone or in combination with polyols, such as glycol and the like may be incorporated into the pharmaceutically acceptable carrier material.

The method of color change of this invention can be sided by any conditioning of the hair which accelerates hair penetration by causing the hair to be more porous. Such treatments include shampooing, prebleaching, adding known hair swelling agents and the like.

In addition, various fillers, buffers, additional solvents, detergents, perfumes, stabilizers and the like may be used in combination with the solution applied to the hair. The use of these various additional ingredients will depend upon the specific mode of application, the specific type of hair texture and dyestuff being used as well as other variables known to those skilled in the art.

The following examples are set forth for the purposes of illustration only and are not to be construed as limitations on the present invention except as set forth in the appended claims. All parts and percentages are by weight unless otherwise indicated.

EXAMPLE I Locks of blonde hair which were previously washed with a commercial shampoo, rinsed clean and dried were treated with an aqueous solution containing 1 per cent ortho-phthalaldehyde. One of the treated locks of hair was washed free of the solution after 5 minutes and another treated lock was washed free of solution after 10 minutes. Neither sample showed color change.

EXAMPLE ll A lock of blonde human hair is treated with an aque ous solution containing 0.2 parts of aminodiphenylamine and .2 parts of o-phthalaldehyde in 100 parts of solution. The solution was allowed to remain on the hair for 4 minutes and then rinsed with warm water. The resultant hair has a rich black color. A lock of hair was similarly treated with an aqueous solution containing only 0.2 parts of paminodiphenylamine per 100 parts of solution. The resultant hair has a pale brown color.

EXAMPLE l1l A lock of human hair is treated with an aqueous alcoholic (80:20) solution containing 0.2 parts of p,- phenylenediamine and 0.2 parts p-phthalaldehyde. The solution is allowed to remain on the hair for 5 minutes and then rinsed with warm water. The resultant hair has a rich black color.

EXAMPLE 1V An emulsion comprising Glycerol monostearate 8.0 Sodium lauryl sulfate 0.25 Propyl paraben 0.1 Methyl paraben 0.15 Water q.s.

is mixed with 0.2 parts of p-diaminoanisole and 0.2 parts of p-phthalaldehyde. The emulsion thus formed is applied to human bonde hair and allowed to remain for 4 minutes. The emulsion is then rinsed off with a commercial shampoo. The color of the hair is black. When TABLE Lemmas v,Time Resultant EXAMPLE VII Blonde hair was rinsed with a 0.01 per cent ammonium hydroxide solution and was then saturated with a 0.2 per cent ortho-phthalaldehyde aqueous-alcoholic (80:20) solution. The solution was allowed to remain on the hair for 4 minutes and then rinsed with water.

I The hair color 'was black. V

a same solution is allowed to remain on the hair for l minute a blue-gray is attained.

EXAMPLE V An aqueous solution containing .2 parts of paminophenol dye with 0.2 parts 1,3-propyldia1dehyde is applied to a lock of human hair and allowed to remain for 4 minutes. The hair is then rinsed with warm water and a commercial shampoo. The resultant hair had a warm brown coloration.

In comparison, an aqueous solution containing 0.2 parts of p-aminophenol dye is applied to human hair as described above. Only a brown tinge resulted.

EXAMPLE VI Locks of blonde hair which have been previously washed with a commercial shampoo, rinsed clean and dried were treated with aqueous solutions containing 0.1 per cent of various nitrogen containing compounds in combination with 0.1 per cent of various dialdehydes as shown in Table l below. The solutions were allowed to remain on the hair for the period of time stated and then rinsed free of the solution with warm water after which time visual observation of color change was made.

EXAMPLE VIII Blonde hair is first shampooed with a composition containing Triethanolamine Lauryl Sulfate l6 parts Myristic Diethanolamine 4 parts Ammonium Hydroxide .01 part Water q.s.

The hair was next dressed with a composition comprising Polyvinyl Pyrrolidone 1.0 part Glycerol 1.0 part o-phthalaldehyde 0.2 part water/ethanol (:20) 7 q.s.

The hair, rinsed after 1 minute, attained a blue-gray color.

It will be understood that it is intended to cover all changes and modifications of the examples of the invention herein chosen for the purposes of illustration which do not constitute departures from the spirit and scope of the invention.

What is claimed is:

l. A method of promoting color change in human hair comprising applying to the hair an aqueous carrier containing dispersed therein from about 0.5 to about 5 parts per parts of composition of a dialdehyde compound selected from the group consisting of ortho, meta, or para-phthalaldehyde and from about 0.1 part to 20 parts per 100 parts of composition of at least one nitrogen containing compound selected from the group consisting of monoalkanolamine, trialkanolamine, C -C alkyl alkanolamine, C,C, dialkyl alkanolamine, C,C alkyl dialkanolamine and ammonium hydroxide, said alkanol radical of said nitrogen containing compound being a C -C alkanol group; allowing the composition to remain on the hair for a period to effect the desired color change and rinsing said spent composition from the hair.

2. The method according to claim 1 wherein the applied composition contains ortho-phthalaldehyde.

3. The method according to claim 1 wherein the nitrogen containing compound is N1-I O1-I.

dialkanolamine,

4. The method according to claim 1 wherein the nitrogen containing compound is tri(C,C alkanol)amine,

5. The method according to claim 1 wherein the nitrogen containing compound is C C alkyl di(C C alkanohamine.

6. A cosmetic hair coloring composition comprising an aqueous carrier containing from about 0.05 part to about 5 parts per 100 parts composition of a dialdehyde compound selected from the group consisting of o-phthalaldehyde, m-phthaladehyde and pphthaladehyde, from about 0.] part to about parts per 100 parts of, composition of at least one nitrogen containing compound selected from the group'consisting of alkanolamine, dialkanolamine, trialkanolamine, alkyl alkanolamine, dialkyl alkanolamine, alkyl dialkanolamine and Nl-LOH, wherein the alkanol groups are C -C alkanol groups and the alkyl groups are C -C groups.

7. The cosmetic hair coloring composition according to claim 6 wherein the dialdehyde is orthophthalaldehyde and the nitrogen containing compound is NH OH.

8. The cosmetic hair coloring composition according to claim 6 wherein the dialdehyde is orthophthalaldehyde and the nitrogen containing compounds are NH OH and C C alkyl di(C,'-C alkanol)amine.

v 9. The cosmetic hair coloring composition according to claim 6 wherein the dialdehyde. is orthophthalaldehyde and the nitrogen containing compound is a C C alkanolamine.

* l= IF 

1. A METHOD OF PROMOTING COLOR CHANGE IN HUMAN HAIR COMPRISING APPLYING TO THE HAIR AN AQUEOUS CARRIER CONTANING DISPERSED THEREIN FROM ABOUT 0.5 TO ABOUT 5 PARTS PER 100 PARTS OF COMPOSITION OF A DIALDEHYDE COMPOUND SELECTED FROM THE GROUP CONSISTING OG ORTHO, META, OR PARA-PHTHALALDEHYDE AND FROM ABOUT 0.1 PART TO 20 PARTS PER 100 PARTS OF COMPOSITION OF AT LEAST ONE NITROGEN CONTAINING COMPOUND SELECTED FROM THE GROUP CONSISTING OF MONOALKANOLAMINE, DIALKANOLAMINE, TRIALKANOLAMINE, C1-C15 ALKYL ALKANOLAMINE, C1-C15 DIALKYL ALKANOLAMINE, C1-C15 ALKYL DIALKANOLAMINE AND AMMONIUM HYDROXIDE, SAID ALKANOL RADICAL OF SAID NITROGEN CONTAINING COMPOUND BEING A C1-C3 ALKANOL GROUP; ALLOWING THE COMPOSITION TO REMAIN ON THE HAIR FOR A PERIOD TO EFFECT THE DESIRED COLOR CHANGE AND RINSING SAID SPENT COMPOSITION FROM THE HAIR.
 2. The method according to claim 1 wherein the applied composition contains ortho-phthalaldehyde.
 3. The method according to claim 1 wherein the nitrogen containing compound is NH4OH.
 4. The method according to claim 1 wherein the nitrogen containing compound is tri(C1-C3 alkanol)amine.
 5. The method according to claim 1 wherein the nitrogen containing compound is C1 - C15 alkyl di(C1-C3alkanol)amine.
 6. A cosmetic hair coloring composition comprising an aqueous carrier containing from about 0.05 part to about 5 parts per 100 parts composition of a dialdehyde compound selected from the group consisting of o-phthalaldehyde, m-phthaladehyde and p-phthaladehyde, from about 0.1 part to about 20 parts per 100 parts of composition of at least one nitrogen containing compound selected from the group consisting of alkanolamine, dialkanolamine, trialkanolamine, alkyl alkanolamine, dialkyl alkanolamine, alkyl dialkanolamine and NH4OH, wherein the alkanol groups are C1-C3 alkanol groups and the alkyl groups are C1-C15 groups.
 7. The cosmetic hair coloring composition according to claim 6 wherein the dialdehyde is ortho-phthalaldehyde and the nitrogen containing compound is NH4OH.
 8. The cosmetic hair coloring composition according to claim 6 wherein the dialdehyde is ortho-phthalaldehyde and the nitrogen containing compounds are NH4OH and C1 - C15 alkyl di(C1-C3 alkanol)amIne.
 9. The cosmetic hair coloring composition according to claim 6 wherein the dialdehyde is ortho-phthalaldehyde and the nitrogen containing compound is a C1 - C3 alkanolamine. 